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Holiday Rentals in Chestertown

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Our top choices for Chestertown holiday rentals

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is €139
includes taxes & fees
14 Jan - 15 Jan
First Floor Studio Apartment in Historic Chestertown

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is €110
includes taxes & fees
5 Jan - 6 Jan
Guest Suite for up to 2 in a Victorian on the Chester River

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is €213
includes taxes & fees
4 Jan - 5 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (94)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"
United States
Edward J.
The price is €176
includes taxes & fees
11 Jan - 12 Jan
Hidden Fells Point Gem / Private Courtyard Patio

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is €223
includes taxes & fees
4 Jan - 5 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Glen Burnie
8.0 out of 10, Very good, (2)
"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"
United States
James D.
The price is €111
includes taxes & fees
2 Jan - 3 Jan
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is €361
includes taxes & fees
3 Jan - 4 Jan
Waterfront Oasis of Annapolis Star

Spacious Private 2BR Suite in Abingdon with Separate Entrance

Spacious Private 2BR Suite in Abingdon with Separate Entrance
2.0 star property
Bel Air South
The price is €113
includes taxes & fees
4 Jan - 5 Jan
Spacious Private 2BR Suite in Abingdon with Separate Entrance

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
Rosedale
9.0 out of 10, Wonderful, (2)
"It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. "
United States
Cathy
The price is €424
includes taxes & fees
4 Jan - 5 Jan
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Historic District
9.6 out of 10, Exceptional, (27)
"Loved this place - well appointed, convenient and great hosts ! Definitely will rent again!"
United States
betsy b.
The price is €274
includes taxes & fees
4 Jan - 5 Jan
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is €271
includes taxes & fees
6 Jan - 7 Jan
Waterfront Retreat with Private Dock and Beach

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (73)
"Great location!"
United States
Burton S.
The price is €299
includes taxes & fees
1 Feb - 2 Feb
Cozy 2br home w/ parking in downtown Annapolis

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is €264
includes taxes & fees
2 Jan - 3 Jan
BAYSIDE BUNGALOW

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (36)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
The price is €275
includes taxes & fees
4 Jan - 5 Jan
Large 2 bedroom house with private parking in a nice neighborhood

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
2.0 star property
Berea
9.6 out of 10, Exceptional, (5)
"Everything was great, easy check in and simple and clean space!!! Amazing thank you"
United States
michael t.
The price is €275
includes taxes & fees
5 Jan - 6 Jan
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (146)
"Our family was in town from all over the US for family wedding. Plenty of room for all of us and had a great time at the large kitchen table sharing meals and playing games."
United States
lynn p.
The price is €517
includes taxes & fees
15 Jan - 16 Jan
5-bedroom vacation home 5 minutes from historic Charlestown

Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Baltimore
10.0 out of 10, Exceptional, (12)
"Everything was wonderful - the boat was just as described, even wit a few extra touches that meant a lot - snacks, water bottles, shampoo/conditioner, plenty of hangers, and the SUPER clean, just to name a few! We would love to stay again! Thank you so much!"
United States
Maggie P.
The price is €468
includes taxes & fees
5 Jan - 6 Jan
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
8.6 out of 10, Excellent, (8)
"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
United States
Jeffrey S.
The price is €304
includes taxes & fees
5 Jan - 6 Jan
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is €491
includes taxes & fees
4 Jan - 5 Jan
Charming Pet-Friendly Stay - Near Bay & Beaches.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Find out more about Chestertown

Everything you need to know about Chestertown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chestertown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestertown holiday rentals we have selected for you start as low as €111 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Chestertown?

Yes, there are holiday rentals in Chestertown close to Crumpton Auction, or you can select a more secluded option if you're looking for a relaxing stay. Chestertown is known for its sporting events and university setting. Make sure you have time to check out the festivals and art during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chestertown offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chestertown?

Expedia has 23 holiday rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Northern Chesapeake Bay and Chesapeake Bay, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Chestertown Historic District and Rolphs Wharf Marina are other places to visit while you're in town.

What are holiday rentals like in Chestertown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestertown. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.